Reaktion #1865

Reaktionsgleichung

1,3-dihydro-4-hydroxy-1,3-dimethyl-2H-indol-2-one

potassium carbonate

dimethylsulfate

→

oil

Ausbeute 86.2%

1,3-Dihydro-4-methoxy-1,3-dimethyl-2H-indol-2-one

Ausbeute 86.2%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   SonstigeThe addition funnel was replaced with a condenser
3. 3
   Temperaturthe slurry was refluxed for 18 hours
4. 4
   FiltrationThe K2CO3 was filtered off
5. 5
   Waschenwashed well with acetone
6. 6
   SonstigeAcetone was evaporated
7. 7
   Sonstigethe residue was purified by column chromatography

Vorschrift

A slurry of 1,3-dihydro-4-hydroxy-1,3-dimethyl-2H-indol-2-one (50 g), milled potassium carbonate (60.1 g) and HPLC grade acetone (400 ml) was mechanically stirred at room temperature as dimethylsulfate (41.4 ml) was added dropwise. The addition funnel was replaced with a condenser and the slurry was refluxed for 18 hours. The K2CO3 was filtered off and washed well with acetone. Acetone was evaporated and the residue was purified by column chromatography to yield 46.5 g of an oil. The oil was dissolved in ether and placed in the refrigerator where, upon standing overnight, the product crystallized, m.p. 73°-74° C.

Quelle